Methylamine → 2-[(2-bromophenyl)-hydrazono]-N-methyl-2-cyanoacetamide

HRID 2375587Notes

Reaction equation

HRID 2375587 reaction equation
C(O[C:4](=[O:17])[C:5](=[N:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Br:16])[C:6]#[N:7])C.[CH3:18][NH2:19]>O>[Br:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][N:8]=[C:5]([C:6]#[N:7])[C:4]([NH:19][CH3:18])=[O:17]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 4084583[(2-Bromophenyl)-hydrazono]-cyanoacetic acid ethyl ester

Product 1

HCID 866130992-[(2-bromophenyl)-hydrazono]-N-methyl-2-cyanoacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[(2-Bromophenyl)-hydrazono]-cyanoacetic acid ethyl ester (15.28 g, 51.60 mmol) was dissolved in 40% methylamine in water (67.5 mL) and stirred at room temperature overnight. The reaction mixture was concentrated to dryness, slurried in diethyl ether, and filtered. After drying under high vacuum at 40° C., the title compound was obtained as a yellow solid (11.16 g, 77%). 1H NMR (300.132 MHz, CDCl3) δ 7.68 (dd, J=8.2, 1.4 Hz, 1H), 7.54 (dd, J=8.1, 1.3 Hz, 1H), 7.35 (t, J=7.9 Hz, 1H), 7.01 (td, J=7.7, 1.5 Hz, 1H), 6.29 (s, 1H), 2.98 (d, J=4.9 Hz, 3H). MS APCI, m/z=281/283 (M+H). HPLC 4.08 min.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. filtrationfiltered
  3. customAfter drying under high vacuum at 40° C.

Sources & evidence

ORD record
ord-a82ec8a6d9694b508ca413e223cdc74f
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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